Ammonium Hydroxide → 6-Quinazolinecarboxylic acid, 1,4-dihydro-2-(2-ethoxy-3-methoxyphenyl)-4-oxo-

HRID 236986Notes

Reaction equation

HRID 236986 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=3[O:21][CH2:22][CH3:23])[O:10][C:9](=O)[C:8]=2[CH:25]=1)([OH:3])=[O:2].[OH-].[NH4+:27]>[OH-].[Na+]>[C:1]([C:4]1[CH:25]=[C:8]2[C:7](=[CH:6][CH:5]=1)[N:12]=[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=1[O:21][CH2:22][CH3:23])[NH:27][C:9]2=[O:10])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 12528360HCID 12528360, compound

Product 1

HCID 1354174066-Quinazolinecarboxylic acid, 1,4-dihydro-2-(2-ethoxy-3-methoxyphenyl)-4-oxo-

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The yield is 5 g of 6-carboxy-2-(2'-ethoxy-3'-methoxy-phenyl)-4H-3,1-benzoxazin-4-one (m.p.=175°-177° C.), which are reacted at room temperature first with 70 ml of 32% ammonium hydroxide for 4 hours and then with 20 ml of 2N NaOH overnight. After acidification with 4N HCl, the precipitate is filtered off and crystallized from ethanol to give 6-carboxy-2-(2'-ethoxy-3'-methoxy-phenyl)-3,4-dihydro-4-oxo-quinazoline (3 g; m.p. 228°-229° C.).

Workup

  1. filtrationAfter acidification with 4N HCl, the precipitate is filtered off
  2. customcrystallized from ethanol

Sources & evidence

ORD record
ord-16dcb12686cf4d7a807b6ddfd4901753
Source dataset
uspto-grants-1979_06
Patent number
US04159330

Reaction notes

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